|Publication number||US4872877 A|
|Application number||US 07/026,631|
|Publication date||Oct 10, 1989|
|Filing date||Mar 17, 1987|
|Priority date||Mar 17, 1987|
|Publication number||026631, 07026631, US 4872877 A, US 4872877A, US-A-4872877, US4872877 A, US4872877A|
|Original Assignee||Dennis T. Grendahl|
|Export Citation||BiBTeX, EndNote, RefMan|
|Patent Citations (9), Referenced by (33), Classifications (25), Legal Events (6)|
|External Links: USPTO, USPTO Assignment, Espacenet|
1. Field of the Invention
This invention relates to the field of foldable or elastomeric implantable intraocular lenses composed primarily of transparent silicone, and more particularly, pertains to a method for incorporating ultraviolet screening agents into such lenses.
2. Description of the Prior Art
Poly (methyl methacrylate), such as Perspex CQ from Imperial Chemical Industries (ICI), has been used for a number of years for intraocular lenses. Early implantable intraocular lenses were designed to replace cataract-damaged natural lenses, and were generally made of poly (methyl methacrylate). Ultraviolet screening agents were later added to the polymeric lens formulations because of concern over possible ultraviolet radiation damage to the retina.
Typical compounds used to impart ultraviolet protection to poly (methyl methacrylate) fall primarily into one of two classes, hydroxybenzophenones and their derivatives, or hydroxybenzotriazoles and their derivatives. These materials are available commercially under a number of different trade names and absorb different wavelengths of ultraviolet radiation depending on their substitute groups. Most of these compounds are effective in blocking transmission of 90% of the ultraviolet radiation below a wavelength of 400 nm when used at concentrations below 1% by weight in a plastic sheet 1 mm thick.
Transparent silicone lenses were developed later because the lenses allowed for insertion through a smaller incision by folding the lens.
Many of the same ultraviolet screening agents may be mixed into the silicone rubber compounds before they are fabricated into lenses and cured. However, in the interests of increased production volume, the silicone lenses are formed in mold cavities with the application of heat. These conditions produce an undesirable yellow color when ultraviolet screening agents are present. The screening agents also retard or inhibit the cure of some types of silicone resulting in undesirable weak and soft lenses. Additionally, when silicone lenses are treated to prevent fogging when immersed in water, some of the screening agents may be lost by leaching from the silicone matrix.
The shortcomings are minimized in the lenses of the present invention which are made by using diffusion to incorporate the ultraviolet screening agent into the lens after it has been shaped and cured.
The lenses themselves are preformed of any silicone material customarily used in their fabrication. Illustrative are McGhan NuSIL MED-6210 A/B, Petrarch Systems PSW 2398 A/B. These materials are all either resin-reinforced dimethyl siloxanes or resin reinforced copolymers of dimethyl and diphenyl siloxanes containing 4-12 percent diphenyl siloxane.
Preferred for use are McGhan NuSIL MED-6210 A/A or Shin-Etsu KE 1935 A/B.
The lenses are made by conventional techniques, ordinarily molding or casting.
The ultraviolet screening agents can be o-hydroxphenyl ketones such as O-hydroxybenzophenones; hydroxybenzotriazoles such as 2-(2-hydroxyphenyl) benzotriazoles; and substituted or unsubstituted phenylformamidines. Preferred for use according to the invention are 2,2'-dihydroxy-4,4'-dimethoxybenzophenone (Uvinul D-49) and 2-(2'-hydroxy-5'-methyl phenyl)benzotriazole (Tinuvin P).
The screening agents can be used alone or in combination.
(The optimum benzotriazole identified to date is 2(3',5'-di-tert-butyl-2'-hydroxyphenyl)-5-chlorobenzotriazole.)
Lenses are made according to the invention by first preparing a solution of a screening agent in an organic liquid. Any liquid may be used provided the liquid will dissolve the required amount of agent, will not significantly degrade the lens material, and is physiologically acceptable. Illustrative are lower alcohols (methanol, ethanol, isopropanol), lower ketones (propanone, butanone), ethyl acetate, tetrahydrofuran, aromatics (benzene, toluene, xylene).
Isopropanol is preferred.
The concentration of screening agent in the the liquid is dictated by the nature of the silicone used to fabricate the lens, and must be such that the solution has a higher concentration of absorber than the lens material. Ordinarily, a concentration of 0.05-0.5%. by weight, will give a solution having the requisite concentration.
A preformed lens is then immersed in the solution, or otherwise brought into contact with it, and is then held at a temperature of 20°-40° C. until the solution and lens reach osmotic equilibrium, determined by the ultraviolet absorption at 400 nm reaching a constant value. This ordinarily takes 2-10 days. The lens is then separated from the solution, rinsed and dried to constant weight, and is then ready for use.
Those skilled in this art will be able to practice the invention more easily after referring to the following illustrative example.
These artisans will no doubt be able to compose numerous variations on the theme disclosed, such as changing the amounts of components slightly but insignificantly from those shown, adding innocuous substances, or substituting equivalent or nearly equivalent components for those shown. All such variations are considered to be within the inventive concept.
A solution is prepared by dissolving 0.0316 g of Uvinul D-49 in the 12.77 ml of isopropanol.
A piece of cured silicone rubber 2 mm thick and weighing 1.3 g is then immersed in the solution for three days at 25° C. It is then removed and dried at 80° C. to constant weight. Its UV absorbance is found to be one absorbance unit at 382 nm. The rubber is colorless and shows no change in hardness.
Various modifications can be made to the present invention without departing from the apparent scope thereof.
|Cited Patent||Filing date||Publication date||Applicant||Title|
|US4021471 *||Apr 18, 1974||May 3, 1977||Givaudan Corporation||Formamidines useful as ultraviolet light absorbers|
|US4189546 *||Dec 5, 1978||Feb 19, 1980||Bausch & Lomb Incorporated||Polysiloxane shaped article for use in biomedical applications|
|US4217038 *||Jun 5, 1978||Aug 12, 1980||Bausch & Lomb Incorporated||Glass coated polysiloxane contact lens|
|US4238524 *||Mar 6, 1978||Dec 9, 1980||American Optical Corporation||Process for identification marking clear plastic articles|
|US4257692 *||Oct 13, 1978||Mar 24, 1981||Essilor International "Cie Generale D'optique||Method of marking ophthalmic lenses of organic material and lenses so marked|
|US4304895 *||Nov 15, 1976||Dec 8, 1981||Wesley-Jessen, Inc.||Ultraviolet absorbing corneal contact lenses|
|US4478876 *||Jan 17, 1983||Oct 23, 1984||General Electric Company||Process of coating a substrate with an abrasion resistant ultraviolet curable composition|
|US4636212 *||Mar 18, 1985||Jan 13, 1987||Optical Radiation Corporation||Ultraviolet radiation absorbing intraocular lens|
|JP13006882A *||Title not available|
|Citing Patent||Filing date||Publication date||Applicant||Title|
|US5026395 *||May 25, 1989||Jun 25, 1991||Canon Kabushiki Kaisha||Intraocular lens having a coating layer and a method for manufacturing the same|
|US5147396 *||Mar 23, 1989||Sep 15, 1992||Hoya Corporation||Intraocular lens|
|US5164462 *||Apr 25, 1991||Nov 17, 1992||Allergan, Inc.||Ultraviolet light absorbing compounds and silicone compositions|
|US5211662 *||Mar 5, 1991||May 18, 1993||Alcon Laboratories, Inc.||Bicomposite intraocular lenses|
|US5352753 *||Nov 2, 1992||Oct 4, 1994||Allergan, Inc.||Ultraviolet light absorbing compounds, silicone compositions and methods for making same|
|US5376737 *||Oct 13, 1992||Dec 27, 1994||Allergan, Inc.||Methods for benefitting polymers|
|US5397848 *||May 21, 1993||Mar 14, 1995||Allergan, Inc.||Enhancing the hydrophilicity of silicone polymers|
|US5466768 *||May 6, 1994||Nov 14, 1995||Allergan, Inc.||Ultraviolet light absorbing compounds, silicone compositions and methods for making same|
|US6244707||Jul 21, 1998||Jun 12, 2001||Wesley Jessen Corporation||UV blocking lenses and material containing benzotriazoles and benzophenones|
|US6441119||Sep 20, 2000||Aug 27, 2002||Hoya Corporation||Optical materials having good ultraviolet absorbability and method for producing them|
|US6448304 *||Sep 20, 2000||Sep 10, 2002||Hoya Corporation||Optical materials having good ultraviolet absorbability and method for producing them|
|US6673888||Feb 12, 2002||Jan 6, 2004||Hoya Corporation||Optical materials having good ultraviolet absorbability and method for producing them|
|US6767934||Mar 16, 2000||Jul 27, 2004||Pharmacia Groningen Bv||Macromolecular compounds|
|US7009025||Jan 5, 2004||Mar 7, 2006||Hoya Corporation||Optical materials having good ultraviolet absorbability and method for producing them|
|US7354980||Mar 14, 2005||Apr 8, 2008||Key Medical Technologies, Inc.||High refractive index polymers for ophthalmic applications|
|US7446157||Dec 7, 2004||Nov 4, 2008||Key Medical Technologies, Inc.||Nanohybrid polymers for ophthalmic applications|
|US7745555||Nov 19, 2007||Jun 29, 2010||Key Medical Technologies, Inc.||Nanohybrid polymers for ophthalmic applications|
|US8048972||Jun 25, 2010||Nov 1, 2011||Key Medical Technologies, Inc.||Nanohybrid polymers for ophthalmic applications|
|US8420753||Oct 13, 2011||Apr 16, 2013||Key Medical Technologies, Inc.||Nanohybrid polymers for ophthalmic applications|
|US9005282||Apr 20, 2007||Apr 14, 2015||Calhoun Vision, Inc.||Intraocular lens system with injectable accommodation material|
|US9056934||Mar 22, 2013||Jun 16, 2015||Key Medical Technologies, Inc.||Nanohybrid polymers for ophthalmic applications|
|US20040141230 *||Jan 5, 2004||Jul 22, 2004||Masahisa Kosaka||Optical materials having good ultraviolet absorbability and method for producing them|
|US20050246018 *||Apr 29, 2005||Nov 3, 2005||Calhoun Vision, Inc.||Injectable accommodation composition|
|US20060122349 *||Dec 7, 2004||Jun 8, 2006||Key Medical Technologies, Inc.||Nanohybrid polymers for ophthalmic applications|
|US20080033547 *||Apr 20, 2007||Feb 7, 2008||Calhoun Vision, Inc||Intraocular lens system with injectable accommodation material|
|US20080064840 *||Nov 19, 2007||Mar 13, 2008||Khalid Mentak||Nanohybrid Polymers for Ophthalmic Applications|
|US20100261858 *||Jun 25, 2010||Oct 14, 2010||Key Medical Technologies, Inc.||Nanohybrid polymers for ophthalmic applications|
|EP1085349A2 *||Sep 12, 2000||Mar 21, 2001||Hoya Corporation||Plastic lenses having good ultraviolet absorbability, and method for the production thereof|
|EP1085349A3 *||Sep 12, 2000||Mar 13, 2002||Hoya Corporation||Plastic lenses having good ultraviolet absorbability, and method for the production thereof|
|WO1992019625A1 *||Mar 25, 1992||Nov 12, 1992||Allergan, Inc.||Ultraviolet light absorbing compounds and silicone compositions|
|WO1994009042A1 *||Oct 6, 1993||Apr 28, 1994||Allergan, Inc.||Methods for benefitting polymers|
|WO1994010588A1 *||Nov 2, 1993||May 11, 1994||Allergan, Inc.||Ultraviolet light absorbing compounds, silicone compositions and methods for making same|
|WO2000055212A1 *||Mar 16, 2000||Sep 21, 2000||Pharmacia Groningen Bv||Macromolecular compounds|
|U.S. Classification||623/6.56, 8/507, 623/901, 8/638, 351/159.04, 351/159.33|
|International Classification||A61F2/16, A61L27/18, A61L27/50, G02B1/04, C08J7/06|
|Cooperative Classification||C08G18/837, A61F2/16, Y10S623/901, A61L27/18, C08J7/065, A61L27/50, A61L2430/16, G02B1/043, A61F2/1616|
|European Classification||A61L27/18, G02B1/04B2, A61F2/16B2, A61L27/50, C08J7/06B|
|Mar 17, 1987||AS||Assignment|
Owner name: SURGIDEV CORPORATION, 5743 THORNWOOD DR., GOLETA,
Free format text: ASSIGNMENT OF ASSIGNORS INTEREST.;ASSIGNOR:TIFFANY, JOHN;REEL/FRAME:004679/0479
Effective date: 19870312
|Mar 18, 1988||AS||Assignment|
Owner name: GRENDAHL, DENNIS T., 2070 SHORELINE DRIVE, ORONO,
Free format text: ASSIGNMENT OF ASSIGNORS INTEREST.;ASSIGNOR:SURGIDEV CORPORATION;REEL/FRAME:004880/0012
Effective date: 19880317
Owner name: GRENDAHL, DENNIS T.,MINNESOTA
Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNOR:SURGIDEV CORPORATION;REEL/FRAME:004880/0012
Effective date: 19880317
|May 11, 1993||REMI||Maintenance fee reminder mailed|
|May 25, 1993||REMI||Maintenance fee reminder mailed|
|Oct 10, 1993||LAPS||Lapse for failure to pay maintenance fees|
|Dec 28, 1993||FP||Expired due to failure to pay maintenance fee|
Effective date: 19891017